Bromochloromethane → HCID 10049185, compound

Participants

Reaction Steps

To a solution of 1-trityl-1,2,3-triazol-4-ylmethylmercaptan (3.00 g: 8.40 mMol.) in dimethylformamide (10 ml) is added sodium hydride (60% dispersion in oil: 370 mg: 9.25 mMol.), and the mixture is stirred for 5 minutes at room temperature. The reaction mixture is added to a solution of bromochloromethane (15 ml) in dimethylformamide (15 ml) at -30° C., and the mixture is stirred at -20° C. to -30° C. for 30 minutes. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and concentrated. To a solution of the residue in acetone (30 ml) is added potassium thioacetate (1.92 g: 16.8 mMol.), and the mixture is stirred at room temperature for 1 hour. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water, dried over sodium sulfate, and concentrated. The residue is purified by silica chromatography (toluene: ethyl acetate=10:1) and crystallized from ether to give 4-acetylthiomethylthiomethyl-1-trityl-1,2,3-triazole (2.65 g) as colorless crystals. Yield: 71%. mp. 106° C.

Provenance & Evidence